Parasiticidal preparations



. Patented Nov. [4, 1944 F UNlTED STATE.

PATE N oFsicE- rsnasmomar. raaranarrons Elbert 0. use, rmie, N. 1., asslgnor to United States Rubber Company poration of New Jersey No Drawing. Application New York, N..Y., a cor- May '6, 1943,

Serial No. 485,885

This invention relates to new and useful improvements in parasiticidal preparations, more particularly to germlcides, that is, fungicides and ,bactericides, and to insecticides, the latter term being considered to include larv'icides and arachnicides, as well as insectifuges and larvifuges. The invention further relates to methods ofprotecting organic material subject to attack by microorganisms, as in the immunizing of seed, andthe mildewprooflng of fabrics and other material.

I have found that 5,6-dichloro-z-cyclohexenedime-1,4 is an eflective germicide and insecticide. The structure of the compound may. be represented as follows:

The. compound and method of preparation are described in BeilsteinsWHandbuch der Organischen Chemie," vol. 7, page 5'73, 4th edition.

The 5,6-dichloro-2-cyclohexenedione-1,4 may be used as a seed protectant and to protect plants or soil from organisms harmful to "seeds and plants. It may also be applied to prevent or retard fungus growth and the formation of, for example, mildew on rope, wood, fur, hair, feathers, cotton, wool, leather, rubber, rubberized or synthetic resin-coated fabrics, and the like. The 5,6-dichloro-2-cyclohexenedione 1,4 may be applied as dust or sprays or in solution in a suitable solvent. It may be applied diluted onundiluted, or mixed with carrier, or other fungicides, germicides or insecticides, fertilizers, hormones, buffering or safening agents.

healthy seedlings, whereas only 14% of the untreated seeds hadgerminated. The seeds and seedlings were observed to be infected with Puthium ultimum which had caused seed and seed- .ling rot, whereas those which were treated with 5,6-dichloro-2-cyclohexenedione-1,4 were found to be free of this disease.

Example II This case illustrates the effectiveness of 5,6-dichloro-2 cyclohexenedlone-1,4 as a bactericide. 5% by weight of 5,6-dichloro-2cyclohexenedlone- 1,4 was suspended in water which contained 2% of Emulphor-EL (believed to be reaction product of fatty acid or fatty acid ester with ethylene oxide) as a dispersing agent. A section of potato was immersed in this suspension and allowed to The following examples are given to illustrate the invention:

Example I Pea seed, variety Perfection, were tumbled with .25% by weight of the 5,6-dichloro-2- cyclohexenedime-1,4 in dust form. The seeds were then planted in soil known to be infested with a number of organisms, including Pythium illtimum. The effectiveness of the fungicide was determined bycomparing the number of treated seeds which germinated and developed into healthy plants with an equal number of untreated seeds planted under the same conditions. Observations made at the end of ten days showed that 68% of the treated seeds had germinated and grown to standat room temperature. No growth of naturally occurring bacteria was observed after thirty days. on the other hand, a section of potato treated in a similar manner with a-2.% solution of Emulphor-EL in water, which solution did not contain a germicide, became heavily over-grown with naturally occurring bacteria within the same period of time.

' Example III The arachnicidal properties of 5,6-dichloro-2- cyclohexenedione-Li are shown by the following test:

1 part by weight of 5,6-diehloro-2-'cyclohexene dime-1,4 was suspended in 200 parts of water which contained /2 part of lflacconal (wetting agent). The dispersion was then sprayed on bean plants heavily infested with red spiders. Counts taken 72 hours after spraying showed that 30% of the spiders had been killed while control plants which hadben sprayed with water containing 25% oi. Nacconal but without the 5,6-dichloro-2-cyclohexenedione-L4 showed 10% dead.

7 Example 1V 2 e then" allowed to stand me three weeks under equal conditions. At the end of this period it was found that very light surface feeding had occurred on the treated samples, whereas very heavy feeding. had occurred on the untreated samples. Furthermore, 55% of the larvae exposed to the treated samples were dead, whereas there was no mortality in thelarvae exposed to the untreated samples. I

Having thus described my invention, what I claim and desire to protect by Letters Patent is:

1. A fungicidal composition comprising a carrier and 5,6-dichloro-2-cyclohexenedione-1,4 as an essential active ingredient.

2. The method of protecting organic material subject to attack by microorganisms which com- 

